Sec Form 4 Filing - Dawe Grahame @ ASPEN INSURANCE HOLDINGS LTD - 2019-02-15

FORM 4 Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940

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1. Name and Address of Reporting Person Dawe Grahame 2. Issuer Name and Ticker or Trading Symbol ASPEN INSURANCE HOLDINGS LTD [ AHL] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) _____ Director _____ 10% Owner X __ Officer (give title below) _____ Other (specify below) Chief Accounting Officer (Last) (First) (Middle) 141 FRONT STREET 3. Date of Earliest Transaction (MM/DD/YY) 02/15/2019 (Street) HAMILTON, D0HM19 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) __ X __ Form filed by One Reporting Person _____ Form filed by More than One Reporting Person (City) (State) (Zip)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned 1.Title of Security (Instr. 3) 2. Transaction Date (MM/DD/YY) 2A. Deemed Execution Date, if any (MM/DD/YY) 3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4) Code V Amount (A) or (D) Price

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities) 1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (MM/DD/YY) 3A. Deemed Execution Date, if any (MM/DD/YY) 4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4, and 5) 6. Date Exercisable and Expiration Date (MM/DD/YY) 7. Title and Amount of Underlying Securities (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4) Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares Phantom Shares (2017 Grant) ( 1 ) 02/15/2019 D( 2 ) 519 ( 3 ) ( 3 ) Ordinary Shares 519 ( 1 ) ( 4 ) 0 D Phantom Shares (2018 Grant) ( 1 ) 02/15/2019 D 1,234 ( 5 ) ( 5 ) Ordinary Shares 1,234 ( 1 ) ( 6 ) 0 D

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Dawe Grahame 141 FRONT STREET HAMILTON, D0HM19 Chief Accounting Officer Signatures /s/Silvia Martinez as Attorney-in-fact for Grahame Dawe 02/20/2019 Signature of Reporting Person Date

Explanation of Responses:

( 1 )Each Phantom Share represents the right to receive the economic equivalent of one of the Issuer's Ordinary Shares. ( 2 )This Form 4 is being filed as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd. ( 3 )At the time of grant on February 10, 2017, the 2017 Phantom Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2017 Phantom Share award was tested annually over a three-year period. All vested 2017 Phantom Shares would have been settled in cash upon the filing of the annual report on Form 10-K for the year ended December 31, 2019. Two thirds of the 2017 Phantom Shares were forfeited based on the Issuer's 2017 and 2018 adjusted annual growth in diluted book value per ordinary share test and one third of the 2017 Phantom Shares vested at target payout levels in connection with the Merger. ( 4 )At the effective time of the Merger, each 2017 Phantom Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2017 Phantom Share. ( 5 )At the time of grant on February 9, 2018, the 2018 Phantom Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2018 Phantom Share award was tested annually over a three-year period. All vested 2018 Phantom Shares would have been settled in cash upon the filing of the annual report on Form 10-K for the year ended December 31, 2020. One third of the 2018 Phantom Shares were forfeited based on the Issuer's 2018 adjusted annual growth in diluted book value per ordinary share test and two thirds of the 2018 Phantom Shares vested at target payout levels in connection with the Merger. ( 6 )At the effective time of the Merger, each 2018 Phantom Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2018 Phantom Share.

Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.

* If the form is filed by more than one reporting person, see Instruction 4(b)(v).

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